# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_200739LT_0m
_database_code_depnum_ccdc_archive 'CCDC 2131034'
loop_
_audit_author_name
_audit_author_address
'Pei-Lin Chen'
;NTHU
Taiwan
;
_audit_update_record             
;
2021-12-27 deposited with the CCDC.	2022-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
1',4-dimethylspiro[benzo[4,5]imidazo[2,1-a]isoindole-11,3'-pyrrolidine]-2',5'-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H15 N3 O2'
_chemical_formula_weight         317.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   18.0754(12)
_cell_length_b                   15.6627(11)
_cell_length_c                   11.5969(6)
_cell_angle_alpha                90
_cell_angle_beta                 91.250(3)
_cell_angle_gamma                90
_cell_volume                     3282.4(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4869
_cell_measurement_theta_min      2.6008
_cell_measurement_theta_max      26.1124

_exptl_crystal_description       acicular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.284
_exptl_crystal_F_000             1328
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6768
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            10299
_diffrn_reflns_av_unetI/netI     0.0650
_diffrn_reflns_av_R_equivalents  0.0471
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.721
_diffrn_reflns_theta_max         26.336
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3328
_reflns_number_gt                2132
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0901P)²+7.0724P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3328
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1152
_refine_ls_R_factor_gt           0.0688
_refine_ls_wR_factor_ref         0.2016
_refine_ls_wR_factor_gt          0.1769
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.016
_refine_ls_shift/su_mean         0.002

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.03635(13) 0.06109(15) 0.90115(19) 0.0331(6) Uani 1 1 d . . . . .
O2 O -0.06838(13) 0.26981(15) 1.1183(2) 0.0346(6) Uani 1 1 d . . . . .
N1 N 0.15285(15) 0.19196(17) 0.9354(2) 0.0254(6) Uani 1 1 d . . . . .
N2 N -0.03185(15) 0.15700(16) 1.0062(2) 0.0241(6) Uani 1 1 d . . . . .
N3 N 0.26768(15) 0.17064(16) 0.8677(2) 0.0258(6) Uani 1 1 d . . . . .
C1 C 0.1976(2) 0.3159(2) 0.6338(3) 0.0338(8) Uani 1 1 d . . . . .
H1 H 0.2113 0.3425 0.5637 0.041 Uiso 1 1 calc R U . . .
C2 C 0.1264(2) 0.3299(2) 0.6758(3) 0.0332(8) Uani 1 1 d . . . . .
H5 H 0.0932 0.3664 0.6345 0.040 Uiso 1 1 calc R U . . .
C3 C 0.10357(19) 0.2912(2) 0.7773(3) 0.0299(8) Uani 1 1 d . . . . .
H6 H 0.0552 0.2995 0.8059 0.036 Uiso 1 1 calc R U . . .
C4 C 0.15534(18) 0.23956(19) 0.8347(3) 0.0242(7) Uani 1 1 d . . . . .
C5 C 0.09936(18) 0.1695(2) 1.0224(3) 0.0278(8) Uani 1 1 d . . . . .
C6 C 0.14664(19) 0.1093(2) 1.0969(3) 0.0274(8) Uani 1 1 d . . . . .
C7 C 0.1265(2) 0.0653(2) 1.1970(3) 0.0313(8) Uani 1 1 d . . . . .
H7 H 0.0790 0.0727 1.2291 0.038 Uiso 1 1 calc R U . . .
C8 C 0.1782(2) 0.0109(2) 1.2473(3) 0.0338(9) Uani 1 1 d . . . . .
H2 H 0.1661 -0.0186 1.3159 0.041 Uiso 1 1 calc R U . . .
C9 C -0.10496(18) 0.1247(2) 0.9747(3) 0.0317(8) Uani 1 1 d . . . . .
H3 H -0.1146 0.1342 0.8922 0.048 Uiso 1 1 calc R U . . .
H14 H -0.1423 0.1548 1.0193 0.048 Uiso 1 1 calc R U . . .
H15 H -0.1073 0.0635 0.9913 0.048 Uiso 1 1 calc R U . . .
C10 C 0.03278(18) 0.1212(2) 0.9670(3) 0.0248(7) Uani 1 1 d . . . . .
C11 C 0.22025(18) 0.1522(2) 0.9479(3) 0.0247(7) Uani 1 1 d . . . . .
C12 C 0.22707(18) 0.2255(2) 0.7941(3) 0.0260(7) Uani 1 1 d . . . . .
C13 C 0.24850(19) 0.2643(2) 0.6917(3) 0.0298(8) Uani 1 1 d . . . . .
H4 H 0.2966 0.2556 0.6625 0.036 Uiso 1 1 calc R U . . .
C14 C 0.21686(18) 0.0977(2) 1.0514(3) 0.0250(7) Uani 1 1 d . . . . .
C15 C 0.2472(2) -0.0017(2) 1.1996(3) 0.0319(8) Uani 1 1 d . . . . .
H11 H 0.2808 -0.0404 1.2358 0.038 Uiso 1 1 calc R U . . .
C16 C 0.26853(19) 0.0413(2) 1.0995(3) 0.0290(8) Uani 1 1 d . . . . .
C17 C 0.3430(2) 0.0261(2) 1.0466(3) 0.0347(8) Uani 1 1 d . . . . .
H8 H 0.3370 0.0219 0.9626 0.052 Uiso 1 1 calc R U . . .
H9 H 0.3641 -0.0273 1.0769 0.052 Uiso 1 1 calc R U . . .
H10 H 0.3763 0.0736 1.0661 0.052 Uiso 1 1 calc R U . . .
C18 C 0.06274(18) 0.2453(2) 1.0848(3) 0.0280(8) Uani 1 1 d . . . . .
H13 H 0.0791 0.2474 1.1667 0.034 Uiso 1 1 calc R U . . .
H12 H 0.0757 0.3000 1.0475 0.034 Uiso 1 1 calc R U . . .
C19 C -0.01952(19) 0.2292(2) 1.0748(3) 0.0252(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.214(4) . ?
O2 C19 1.208(4) . ?
N1 C11 1.373(4) . ?
N1 C4 1.387(4) . ?
N1 C5 1.455(4) . ?
N2 C10 1.382(4) . ?
N2 C19 1.397(4) . ?
N2 C9 1.454(4) . ?
N3 C11 1.310(4) . ?
N3 C12 1.407(4) . ?
C1 C13 1.387(5) . ?
C1 C2 1.403(5) . ?
C1 H1 0.9500 . ?
C2 C3 1.395(5) . ?
C2 H5 0.9500 . ?
C3 C4 1.394(5) . ?
C3 H6 0.9500 . ?
C4 C12 1.407(5) . ?
C5 C6 1.529(5) . ?
C5 C18 1.547(4) . ?
C5 C10 1.549(4) . ?
C6 C14 1.397(5) . ?
C6 C7 1.404(4) . ?
C7 C8 1.384(5) . ?
C7 H7 0.9500 . ?
C8 C15 1.389(5) . ?
C8 H2 0.9500 . ?
C9 H3 0.9800 . ?
C9 H14 0.9800 . ?
C9 H15 0.9800 . ?
C11 C14 1.476(4) . ?
C12 C13 1.397(4) . ?
C13 H4 0.9500 . ?
C14 C16 1.392(5) . ?
C15 C16 1.404(5) . ?
C15 H11 0.9500 . ?
C16 C17 1.511(5) . ?
C17 H8 0.9800 . ?
C17 H9 0.9800 . ?
C17 H10 0.9800 . ?
C18 C19 1.510(5) . ?
C18 H13 0.9900 . ?
C18 H12 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 C4 106.7(3) . . ?
C11 N1 C5 114.8(3) . . ?
C4 N1 C5 138.4(3) . . ?
C10 N2 C19 113.0(3) . . ?
C10 N2 C9 123.1(3) . . ?
C19 N2 C9 123.9(3) . . ?
C11 N3 C12 103.0(3) . . ?
C13 C1 C2 121.8(3) . . ?
C13 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 121.0(3) . . ?
C3 C2 H5 119.5 . . ?
C1 C2 H5 119.5 . . ?
C2 C3 C4 116.6(3) . . ?
C2 C3 H6 121.7 . . ?
C4 C3 H6 121.7 . . ?
N1 C4 C3 132.8(3) . . ?
N1 C4 C12 104.2(3) . . ?
C3 C4 C12 123.0(3) . . ?
N1 C5 C6 99.8(3) . . ?
N1 C5 C18 115.9(3) . . ?
C6 C5 C18 116.7(3) . . ?
N1 C5 C10 110.7(2) . . ?
C6 C5 C10 110.6(3) . . ?
C18 C5 C10 103.5(3) . . ?
C14 C6 C7 120.2(3) . . ?
C14 C6 C5 111.6(3) . . ?
C7 C6 C5 128.2(3) . . ?
C8 C7 C6 117.7(3) . . ?
C8 C7 H7 121.1 . . ?
C6 C7 H7 121.1 . . ?
C7 C8 C15 121.6(3) . . ?
C7 C8 H2 119.2 . . ?
C15 C8 H2 119.2 . . ?
N2 C9 H3 109.5 . . ?
N2 C9 H14 109.5 . . ?
H3 C9 H14 109.5 . . ?
N2 C9 H15 109.5 . . ?
H3 C9 H15 109.5 . . ?
H14 C9 H15 109.5 . . ?
O1 C10 N2 125.4(3) . . ?
O1 C10 C5 126.0(3) . . ?
N2 C10 C5 108.6(3) . . ?
N3 C11 N1 114.7(3) . . ?
N3 C11 C14 138.1(3) . . ?
N1 C11 C14 107.2(3) . . ?
C13 C12 C4 119.4(3) . . ?
C13 C12 N3 129.2(3) . . ?
C4 C12 N3 111.4(3) . . ?
C1 C13 C12 118.2(3) . . ?
C1 C13 H4 120.9 . . ?
C12 C13 H4 120.9 . . ?
C16 C14 C6 122.5(3) . . ?
C16 C14 C11 130.8(3) . . ?
C6 C14 C11 106.6(3) . . ?
C8 C15 C16 121.8(3) . . ?
C8 C15 H11 119.1 . . ?
C16 C15 H11 119.1 . . ?
C14 C16 C15 116.2(3) . . ?
C14 C16 C17 122.3(3) . . ?
C15 C16 C17 121.5(3) . . ?
C16 C17 H8 109.5 . . ?
C16 C17 H9 109.5 . . ?
H8 C17 H9 109.5 . . ?
C16 C17 H10 109.5 . . ?
H8 C17 H10 109.5 . . ?
H9 C17 H10 109.5 . . ?
C19 C18 C5 105.4(3) . . ?
C19 C18 H13 110.7 . . ?
C5 C18 H13 110.7 . . ?
C19 C18 H12 110.7 . . ?
C5 C18 H12 110.7 . . ?
H13 C18 H12 108.8 . . ?
O2 C19 N2 123.7(3) . . ?
O2 C19 C18 127.4(3) . . ?
N2 C19 C18 108.9(3) . . ?

_refine_diff_density_max         1.131
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.069

_shelxl_version_number           2014/6

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_200218lt_0m_a_pl
_database_code_depnum_ccdc_archive 'CCDC 2133408'
loop_
_audit_author_name
_audit_author_address
'Pei-Lin Chen'
;NTHU
Taiwan
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-08-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        
(3aR,13aS)-2-methyl-3a,13a-dihydro-1H-benzo[4,5]imidazo[2,1-a]pyrrolo[3,4-c]isoquinoline-1,3(2H)-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H13 N3 O2'
_chemical_formula_weight         303.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.2326(10)
_cell_length_b                   8.5326(5)
_cell_length_c                   20.3607(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2820.1(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7659
_cell_measurement_theta_min      2.3613
_cell_measurement_theta_max      26.1493

_exptl_crystal_description       tabular
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             1264
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5458
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            18944
_diffrn_reflns_av_unetI/netI     0.0454
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.000
_diffrn_reflns_theta_max         26.452
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2877
_reflns_number_gt                2293
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+33.0174P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2877
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1653
_refine_ls_R_factor_gt           0.1443
_refine_ls_wR_factor_ref         0.3365
_refine_ls_wR_factor_gt          0.3270
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0953(4) 0.2124(9) 0.6047(3) 0.0330(17) Uani 1 1 d . . . . .
C2 C 0.0940(5) 0.1404(12) 0.6665(4) 0.053(3) Uani 1 1 d . . . . .
H2 H 0.0535 0.0638 0.6765 0.064 Uiso 1 1 calc R U . . .
C3 C 0.1520(5) 0.1817(16) 0.7124(4) 0.075(4) Uani 1 1 d . . . . .
H3 H 0.1526 0.1305 0.7539 0.090 Uiso 1 1 calc R U . . .
C4 C 0.2103(5) 0.2988(14) 0.6988(4) 0.059(3) Uani 1 1 d . . . . .
H4 H 0.2493 0.3255 0.7317 0.070 Uiso 1 1 calc R U . . .
C5 C 0.2130(4) 0.3768(13) 0.6391(3) 0.049(3) Uani 1 1 d . . . . .
H5 H 0.2526 0.4559 0.6301 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1544(4) 0.3321(10) 0.5936(3) 0.0353(18) Uani 1 1 d . . . . .
C7 C 0.1743(4) 0.5166(9) 0.4974(3) 0.0280(15) Uani 1 1 d . . . . .
H7 H 0.1817 0.6050 0.5291 0.034 Uiso 1 1 calc R U . . .
C8 C 0.2598(4) 0.4694(11) 0.4702(4) 0.0364(18) Uani 1 1 d . . . . .
C9 C 0.1952(5) 0.6114(11) 0.3887(4) 0.0397(19) Uani 1 1 d . . . . .
C10 C 0.1266(4) 0.5759(8) 0.4380(3) 0.0259(14) Uani 1 1 d . . . . .
H10 H 0.0989 0.6766 0.4501 0.031 Uiso 1 1 calc R U . . .
C11 C 0.0628(4) 0.4663(10) 0.4091(3) 0.0294(16) Uani 1 1 d . . . . .
C12 C 0.0273(4) 0.5005(11) 0.3481(3) 0.040(2) Uani 1 1 d . . . . .
H12 H 0.0448 0.5891 0.3236 0.048 Uiso 1 1 calc R U . . .
C13 C -0.0346(5) 0.4014(13) 0.3240(4) 0.052(3) Uani 1 1 d . . . . .
H13 H -0.0577 0.4223 0.2821 0.063 Uiso 1 1 calc R U . . .
C14 C -0.0629(4) 0.2747(13) 0.3593(4) 0.051(3) Uani 1 1 d . . . . .
H14 H -0.1061 0.2113 0.3424 0.061 Uiso 1 1 calc R U . . .
C15 C -0.0281(4) 0.2407(11) 0.4194(4) 0.040(2) Uani 1 1 d . . . . .
H15 H -0.0463 0.1520 0.4436 0.048 Uiso 1 1 calc R U . . .
C16 C 0.0348(4) 0.3377(9) 0.4450(3) 0.0292(16) Uani 1 1 d . . . . .
C17 C 0.0699(4) 0.2987(10) 0.5093(3) 0.0299(16) Uani 1 1 d . . . . .
C18 C 0.3431(5) 0.5459(10) 0.3711(4) 0.046(2) Uani 1 1 d . . . . .
H18A H 0.3320 0.5007 0.3277 0.069 Uiso 1 1 calc R U . . .
H18B H 0.3858 0.4842 0.3932 0.069 Uiso 1 1 calc R U . . .
H18C H 0.3621 0.6542 0.3660 0.069 Uiso 1 1 calc R U . . .
N1 N 0.0437(3) 0.1948(8) 0.5513(3) 0.0330(14) Uani 1 1 d . . . . .
N2 N 0.1361(3) 0.3859(7) 0.5315(2) 0.0258(13) Uani 1 1 d . . . . .
N3 N 0.2676(3) 0.5436(8) 0.4104(3) 0.0344(15) Uani 1 1 d . . . . .
O1 O 0.3099(3) 0.3883(7) 0.4962(3) 0.0417(14) Uani 1 1 d . . . . .
O2 O 0.1891(4) 0.6865(7) 0.3381(3) 0.0503(17) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.381(9) . ?
C1 C2 1.399(11) . ?
C1 C6 1.420(11) . ?
C2 C3 1.373(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.404(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.381(10) . ?
C5 H5 0.9500 . ?
C6 N2 1.377(9) . ?
C7 N2 1.453(9) . ?
C7 C10 1.523(9) . ?
C7 C8 1.548(9) . ?
C7 H7 1.0000 . ?
C8 O1 1.192(9) . ?
C8 N3 1.377(10) . ?
C9 O2 1.217(10) . ?
C9 N3 1.382(10) . ?
C9 C10 1.530(9) . ?
C10 C11 1.514(10) . ?
C10 H10 1.0000 . ?
C11 C16 1.395(11) . ?
C11 C12 1.399(9) . ?
C12 C13 1.402(12) . ?
C12 H12 0.9500 . ?
C13 C14 1.377(14) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(12) . ?
C14 H14 0.9500 . ?
C15 C16 1.414(10) . ?
C15 H15 0.9500 . ?
C16 C17 1.466(9) . ?
C17 N1 1.304(9) . ?
C17 N2 1.383(9) . ?
C18 N3 1.465(8) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 C1 C2 130.6(8) . . ?
N1 C1 C6 111.3(6) . . ?
C2 C1 C6 118.0(8) . . ?
C3 C2 C1 119.4(9) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 120.6(8) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 122.4(8) . . ?
C5 C4 H4 118.8 . . ?
C3 C4 H4 118.8 . . ?
C6 C5 C4 115.7(9) . . ?
C6 C5 H5 122.1 . . ?
C4 C5 H5 122.1 . . ?
N2 C6 C5 132.3(8) . . ?
N2 C6 C1 103.9(6) . . ?
C5 C6 C1 123.8(7) . . ?
N2 C7 C10 114.6(5) . . ?
N2 C7 C8 110.8(6) . . ?
C10 C7 C8 105.0(5) . . ?
N2 C7 H7 108.8 . . ?
C10 C7 H7 108.8 . . ?
C8 C7 H7 108.8 . . ?
O1 C8 N3 126.7(6) . . ?
O1 C8 C7 127.1(7) . . ?
N3 C8 C7 106.2(6) . . ?
O2 C9 N3 124.0(7) . . ?
O2 C9 C10 126.9(7) . . ?
N3 C9 C10 109.0(6) . . ?
C11 C10 C7 116.8(6) . . ?
C11 C10 C9 111.4(6) . . ?
C7 C10 C9 102.5(5) . . ?
C11 C10 H10 108.6 . . ?
C7 C10 H10 108.6 . . ?
C9 C10 H10 108.6 . . ?
C16 C11 C12 119.6(7) . . ?
C16 C11 C10 120.4(6) . . ?
C12 C11 C10 119.9(7) . . ?
C11 C12 C13 118.7(8) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 122.0(7) . . ?
C14 C13 H13 119.0 . . ?
C12 C13 H13 119.0 . . ?
C13 C14 C15 119.4(7) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C16 120.0(9) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C11 C16 C15 120.2(7) . . ?
C11 C16 C17 121.3(6) . . ?
C15 C16 C17 118.5(7) . . ?
N1 C17 N2 113.9(6) . . ?
N1 C17 C16 127.9(6) . . ?
N2 C17 C16 118.2(7) . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 N1 C1 104.2(6) . . ?
C6 N2 C17 106.8(6) . . ?
C6 N2 C7 127.0(6) . . ?
C17 N2 C7 126.1(6) . . ?
C8 N3 C9 113.4(6) . . ?
C8 N3 C18 124.4(7) . . ?
C9 N3 C18 122.1(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -178.3(8) . . . . ?
C6 C1 C2 C3 -3.4(12) . . . . ?
C1 C2 C3 C4 2.3(14) . . . . ?
C2 C3 C4 C5 -0.5(15) . . . . ?
C3 C4 C5 C6 0.0(13) . . . . ?
C4 C5 C6 N2 177.0(8) . . . . ?
C4 C5 C6 C1 -1.3(12) . . . . ?
N1 C1 C6 N2 0.2(8) . . . . ?
C2 C1 C6 N2 -175.7(6) . . . . ?
N1 C1 C6 C5 178.9(7) . . . . ?
C2 C1 C6 C5 3.0(11) . . . . ?
N2 C7 C8 O1 -39.0(11) . . . . ?
C10 C7 C8 O1 -163.2(8) . . . . ?
N2 C7 C8 N3 142.8(6) . . . . ?
C10 C7 C8 N3 18.5(8) . . . . ?
N2 C7 C10 C11 -18.6(8) . . . . ?
C8 C7 C10 C11 103.1(7) . . . . ?
N2 C7 C10 C9 -140.6(6) . . . . ?
C8 C7 C10 C9 -18.9(8) . . . . ?
O2 C9 C10 C11 68.1(11) . . . . ?
N3 C9 C10 C11 -111.9(7) . . . . ?
O2 C9 C10 C7 -166.2(9) . . . . ?
N3 C9 C10 C7 13.8(8) . . . . ?
C7 C10 C11 C16 16.2(9) . . . . ?
C9 C10 C11 C16 133.4(7) . . . . ?
C7 C10 C11 C12 -168.6(6) . . . . ?
C9 C10 C11 C12 -51.3(8) . . . . ?
C16 C11 C12 C13 -1.5(10) . . . . ?
C10 C11 C12 C13 -176.8(6) . . . . ?
C11 C12 C13 C14 1.9(11) . . . . ?
C12 C13 C14 C15 -1.9(12) . . . . ?
C13 C14 C15 C16 1.5(11) . . . . ?
C12 C11 C16 C15 1.1(10) . . . . ?
C10 C11 C16 C15 176.4(6) . . . . ?
C12 C11 C16 C17 -179.5(6) . . . . ?
C10 C11 C16 C17 -4.2(9) . . . . ?
C14 C15 C16 C11 -1.1(10) . . . . ?
C14 C15 C16 C17 179.4(6) . . . . ?
C11 C16 C17 N1 171.2(7) . . . . ?
C15 C16 C17 N1 -9.4(11) . . . . ?
C11 C16 C17 N2 -4.9(9) . . . . ?
C15 C16 C17 N2 174.6(6) . . . . ?
N2 C17 N1 C1 -0.3(8) . . . . ?
C16 C17 N1 C1 -176.5(7) . . . . ?
C2 C1 N1 C17 175.3(8) . . . . ?
C6 C1 N1 C17 0.0(8) . . . . ?
C5 C6 N2 C17 -178.8(8) . . . . ?
C1 C6 N2 C17 -0.3(7) . . . . ?
C5 C6 N2 C7 -3.1(12) . . . . ?
C1 C6 N2 C7 175.5(6) . . . . ?
N1 C17 N2 C6 0.4(8) . . . . ?
C16 C17 N2 C6 177.0(6) . . . . ?
N1 C17 N2 C7 -175.5(6) . . . . ?
C16 C17 N2 C7 1.2(9) . . . . ?
C10 C7 N2 C6 -164.2(6) . . . . ?
C8 C7 N2 C6 77.3(8) . . . . ?
C10 C7 N2 C17 10.8(9) . . . . ?
C8 C7 N2 C17 -107.7(7) . . . . ?
O1 C8 N3 C9 171.4(9) . . . . ?
C7 C8 N3 C9 -10.3(9) . . . . ?
O1 C8 N3 C18 -5.7(13) . . . . ?
C7 C8 N3 C18 172.6(7) . . . . ?
O2 C9 N3 C8 177.8(8) . . . . ?
C10 C9 N3 C8 -2.3(10) . . . . ?
O2 C9 N3 C18 -5.0(13) . . . . ?
C10 C9 N3 C18 174.9(7) . . . . ?

_refine_diff_density_max         0.425
_refine_diff_density_min         -0.563
_refine_diff_density_rms         0.119

_shelxl_version_number           2014/6

